Bromine → 2-(3-broMo-2,6-diMethylphenyl)acetic acid

HRID 1183854Notes

Reaction equation

HRID 1183854 reaction equation
[Br:1]Br.[CH3:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH3:10])[C:5]=1[CH2:11][C:12]([OH:14])=[O:13]>C(O)(=O)C.CC1CCCCC1>[Br:1][C:7]1[C:6]([CH3:10])=[C:5]([CH2:11][C:12]([OH:14])=[O:13])[C:4]([CH3:3])=[CH:9][CH:8]=1

Participants

5

Reactant 2

HCID 24408BromineHCID 198401152-(2,6-Dimethylphenyl)acetic acid

Product 1

HCID 529158182-(3-broMo-2,6-diMethylphenyl)acetic acid

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 7962MethylcyclohexaneSolvent

Conditions

Temperature
45 °C

Procedure

At 45° C., a solution of 62.5 g [391 mmol] of bromine in 120 ml of glacial acetic acid is added dropwise over a period of 1 hour to a solution of 47.6 g [290 mmol] of 2,6-dimethylphenylacetic acid in 300 ml of glacial acetic acid. The reaction mixture is then stirred at 45° C. for another 16 hours and concentrated on a rotary evaporator. The solid obtained is stirred in 180 ml of methylcyclohexane at room temperature for 4 hours. After filtration, the residue is washed twice with in each case 60 ml of methylcyclohexane and then dried. This gives 64.9 g of a solid. GC(sil.) analysis: 97.7% pure (89.9% of theory).

Workup

  1. concentrationconcentrated on a rotary evaporator
  2. customThe solid obtained
  3. filtrationAfter filtration
  4. washthe residue is washed twice with in each case 60 ml of methylcyclohexane
  5. customdried

Sources & evidence

ORD record
ord-4d922dcfb0a048f28261527f83e3b875
Source dataset
uspto-grants-2014_03
Patent number
US08664428B2

Reaction notes

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